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A good time to try it: This is a gentle massage, so it's ideal to start with before you move onto raunchier massage. Give him a head massage first to get him relaxed and in the mood. Head massage is perfect for beginners: it's quick and easy and gets you used to physical contact.
Tip: To make the massage more erotic, make small circular movements on his scalp, which contains lots of sexual stimulation spots.
Note: The ear is a very sensitive and highly erogenous area that can send shivers of pleasure through the body when stimulated. Explore with your tongue or just hot breath, but beware: some people can't bear being touched too close to their ear. Stop at the first sign that he's not enjoying it!
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